HRP20211782T1 - Derivati indola kao inhibitori replikacije denga virusa - Google Patents
Derivati indola kao inhibitori replikacije denga virusa Download PDFInfo
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- HRP20211782T1 HRP20211782T1 HRP20211782TT HRP20211782T HRP20211782T1 HR P20211782 T1 HRP20211782 T1 HR P20211782T1 HR P20211782T T HRP20211782T T HR P20211782TT HR P20211782 T HRP20211782 T HR P20211782T HR P20211782 T1 HRP20211782 T1 HR P20211782T1
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- Croatia
- Prior art keywords
- general formula
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- compound
- och3
- formula
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Links
- 150000002475 indoles Chemical class 0.000 title claims 7
- 208000001490 Dengue Diseases 0.000 title claims 3
- 206010012310 Dengue fever Diseases 0.000 title claims 3
- 208000025729 dengue disease Diseases 0.000 title claims 3
- 229940123627 Viral replication inhibitor Drugs 0.000 title 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 8
- 239000003153 chemical reaction reagent Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000012453 solvate Substances 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- TUHNRCPWPMJXQN-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenyl)acetic acid Chemical compound COC1=CC(F)=CC=C1CC(O)=O TUHNRCPWPMJXQN-UHFFFAOYSA-N 0.000 claims 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
- RHGROLHJIHDMPH-UHFFFAOYSA-N 2-(4-fluoro-2-methoxyphenyl)acetyl chloride Chemical compound FC1=CC(=C(C=C1)CC(=O)Cl)OC RHGROLHJIHDMPH-UHFFFAOYSA-N 0.000 claims 1
- XBZBDCOVNQRWPT-UHFFFAOYSA-N 3-methoxy-5-methylsulfonylaniline Chemical compound COC1=CC(N)=CC(S(C)(=O)=O)=C1 XBZBDCOVNQRWPT-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 241000725619 Dengue virus Species 0.000 claims 1
- 239000003443 antiviral agent Substances 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 230000031709 bromination Effects 0.000 claims 1
- 238000005893 bromination reaction Methods 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/4045—Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Claims (10)
1. Spoj s formulom (I)
[image]
njegov stereo-izomerni oblik, farmaceutski prihvatljiva sol, solvat ili polimorf; navedeni spoj je odabran iz skupine pri čemu:
R1 je F, R2 je F, CH3 ili OCH3 i R3 je H,
R1 je H, R2 je Cl ili F i R3 je CH3,
R1 je CH3, R2 je OCH3, F ili H i R3 =H,
R1 je H, R2 je Cl ili F i R3 je H,
R1 je CH3, R2 je H i R3 je F,
R1 je F, R2 je H i R3 je CH3,
R1 je H, R2 je OCH3 i R3 je H ili Cl,
R1 je H, R2 je F i R3 je F,
R1 je CF3 ili OCF3, R2 je H i R3 je H,
R1 je Cl, R2 je OCH3 i R3 je H.
2. Spoj ili njegov stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 naznačen time što je navedeni spoj odabran iz skupine koji čine:
[image]
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.
3. Farmaceutski pripravak naznačen time što sadrži spoj s formulom (I) ili njegov stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 ili 2 zajedno s jednom ili više farmaceutski prihvatljivih pomoćnih tvari, razrjeđivača ili nosača.
4. Spoj s formulom (I) ili njegov stereo-izomerni oblik, farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 ili farmaceutski pripravak prema patentnom zahtjevu 3 naznačen time što je za uporabu kao lijek.
5. Spoj s formulom (I) ili njegov stereo-izomerni oblik, farmaceutski prihvatljiva sol, solvat ili polimorf prema patentnom zahtjevu 1 ili farmaceutski pripravak prema patentnom zahtjevu 3 naznačen time što je za uporabu u liječenju denga groznice.
6. Spoj predstavljen sljedećom strukturnom formulom (I)
[image]
stereo-izomerni oblik, njegova farmaceutski prihvatljiva sol, solvat ili polimorf; navedeni spoj je odabran iz skupine pri čemu:
R1 je F, R2 je F, CH3 ili OCH3 i R3 je H,
R1 je H, R2 je Cl ili F i R3 je CH3,
R1 je CH3, R2 je OCH3, F ili H i R3 =H,
R1 je H, R2 je Cl ili F i R3 je H,
R1 je CH3, R2 je H i R3 je F,
R1 je F, R2 je H i R3 je CH3,
R1 je H, R2 je OCH3 i R3 je H ili Cl,
R1 je H, R2 je F i R3 je F,
R1 je CF3 ili OCF3, R2 je H i R3 je H,
R1 je Cl, R2 je OCH3 i R3 je H
naznačen time što je za uporabu u inhibiciji replikacije virusa denga groznice u biološkom uzorku ili pacijentu.
7. Spoj za uporabu prema patentnom zahtjevu 6 naznačen time što nadalje obuhvaća istodobnu primjenu dodatnog terapeutskog sredstva.
8. Spoj za uporabu prema patentnom zahtjevu 7 naznačen time što je navedeno dodatno terapeutsko sredstvo odabrano od antivirusnog sredstva ili cjepiva protiv denga groznice, ili oboje.
9. Postupak za sintezu spojeva formule (I) prema zahtjevu 1 ili 2 naznačen time što obuhvaća korake:
a) pretvaranje 2-(4-fluor-2-metoksifenil)octene kiseline (II) u odgovarajući 2-(4-fluor-2-metoksifenil)acetil klorid (III) s reagensom za kloriranje;
b) Friedel-Craftsovu reakciju kiselog klorida (III) sa supstituiranim indolom opće formule (IV) izvedenu upotrebom Lewisovog kiselog reagensa u prikladnom otapalu i pod prikladnim reakcijskim uvjetima, kako bi se dobio 3-acilirani indol opće formule (V), pri čemu R1, R2 i R3 imaju isto značenje kao u zahtjevu 1;
c) bromiranje (V) s reagensom u prikladnom otapalu kako bi se dobili spojevi opće formule (VI);
d) reakciju spojeva opće formule (VI) s 3-metoksi-5-(metilsulfonil)-anilinom (VII) u prikladnom otapalu i tipično korištenjem baze za dobivanje spojeva opće formule I kao racemskih smjesa;
e) kiralno odvajanje spojeva opće formule I kako bi se dobili enantiomeri A i B opće formule I
[image]
10. Postupak prema patentnom zahtjevu 9, naznačen time što se međuprodukt opće formule (V) priprema slijedeći korake:
i) pretvaranje supstituiranog indola opće formule (IV) u N-zaštićeni međuprodukt opće formule (VIII) korištenjem reagensa u prisutnosti baze, pri čemu PG je zaštitna skupina, i R1, R2 i R3 imaju isto značenje kao u zahtjevu 1;
ii) Friedel-Craftsovu reakciju supstituiranog indola opće formule (VIII) s kiselim kloridom (III) izvedenu upotrebom Lewisovog kiselog reagensa u prikladnom otapalu i pod prikladnim reakcijskim uvjetima, kako bi se dobio 3-acilirani indol opće formule (IX);
iii) uklanjanje indol-N zaštitne skupine međuprodukta opće formule (IX) s reagensom u smjesi otapala i na prikladnoj reakcijskoj temperaturi da se dobije 3-acilirani indol opće formule (V)
[image]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15151481 | 2015-01-16 | ||
| EP16700810.1A EP3244886B1 (en) | 2015-01-16 | 2016-01-15 | Indole derivatives as dengue viral replication inhibitors |
| PCT/EP2016/050715 WO2016113371A1 (en) | 2015-01-16 | 2016-01-15 | Indole derivatives as dengue viral replication inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211782T1 true HRP20211782T1 (hr) | 2022-03-04 |
Family
ID=52345130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211782TT HRP20211782T1 (hr) | 2015-01-16 | 2016-01-15 | Derivati indola kao inhibitori replikacije denga virusa |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US10029984B2 (hr) |
| EP (1) | EP3244886B1 (hr) |
| JP (1) | JP6830438B2 (hr) |
| KR (1) | KR102509848B1 (hr) |
| CN (1) | CN107428685B (hr) |
| AR (1) | AR103412A1 (hr) |
| AU (1) | AU2016208015B2 (hr) |
| BR (1) | BR112017015123B1 (hr) |
| CA (1) | CA2972329C (hr) |
| CL (1) | CL2017001822A1 (hr) |
| DK (1) | DK3244886T3 (hr) |
| EA (1) | EA032362B1 (hr) |
| ES (1) | ES2904575T3 (hr) |
| HK (2) | HK1246688A1 (hr) |
| HR (1) | HRP20211782T1 (hr) |
| HU (1) | HUE057299T2 (hr) |
| IL (1) | IL253434B (hr) |
| JO (1) | JOP20150335B1 (hr) |
| LT (1) | LT3244886T (hr) |
| MA (1) | MA41341A (hr) |
| MX (1) | MX2017009309A (hr) |
| MY (1) | MY187068A (hr) |
| PH (1) | PH12017501272A1 (hr) |
| SG (1) | SG11201705760XA (hr) |
| SI (1) | SI3244886T1 (hr) |
| TW (1) | TWI700274B (hr) |
| UA (1) | UA123002C2 (hr) |
| UY (1) | UY36518A (hr) |
| WO (1) | WO2016113371A1 (hr) |
| ZA (1) | ZA201704783B (hr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201116559D0 (en) | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB201305376D0 (en) | 2013-03-25 | 2013-05-08 | Univ Leuven Kath | Novel viral replication inhibitors |
| JOP20160086B1 (ar) * | 2015-05-08 | 2021-08-17 | 2 Katholieke Univ Leuven Ku Leuven Research And Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JO3633B1 (ar) * | 2015-09-16 | 2020-08-27 | Katholieke Univ Leuven Ku Leuven Research & Development | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20160198B1 (ar) | 2015-09-16 | 2022-03-14 | Janssen Pharmaceuticals Inc | مشتقات اندول مستبدلة احاديا او ثنائيا بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| CR20180495A (es) | 2016-03-31 | 2018-12-06 | Univ Leuven Kath | Deribados de indol sustituidos como inhibidores de replicación viral del dengue |
| BR112018069601A2 (pt) | 2016-03-31 | 2019-01-29 | Janssen Pharmaceuticals Inc | derivados de indolina substituídos como inibidores da replicação viral da dengue |
| MA44502A (fr) | 2016-04-01 | 2019-02-06 | Janssen Pharmaceuticals Inc | Dérivés d'indole substitués utilisés en tant qu'inhibiteurs de réplication du virus de la dengue |
| JOP20170069B1 (ar) | 2016-04-01 | 2021-08-17 | 1 Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180026A1 (ar) * | 2017-03-31 | 2019-01-30 | Univ Leuven Kath | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| JOP20180025B1 (ar) | 2017-03-31 | 2021-08-17 | Janssen Pharmaceuticals Inc | مشتقات اندولين مستبدلة بصفتها مانعات للتكاثر الفيروسي لحمى الفنك |
| KR102625988B1 (ko) | 2017-05-22 | 2024-01-16 | 얀센 파마슈티칼즈, 인코포레이티드 | 뎅기 바이러스 복제 억제제로서의 치환 인돌린 유도체 |
| IL270727B2 (en) | 2017-05-22 | 2023-03-01 | Janssen Pharmaceuticals Inc | Transduced indulin derivatives as inhibitors of dengue virus replication |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2928645A1 (fr) * | 2008-03-14 | 2009-09-18 | Sanofi Aventis Sa | Nouveaux derives de carbazole inhibiteurs d'hsp90, compositions les contenant et utilisation |
| EP2326631A4 (en) * | 2008-08-18 | 2012-03-21 | Univ Yale | MODULATORS OF MIF |
| GB201116559D0 (en) * | 2011-09-26 | 2011-11-09 | Univ Leuven Kath | Novel viral replication inhibitors |
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2015
- 2015-12-29 JO JOP/2015/0335A patent/JOP20150335B1/ar active
-
2016
- 2016-01-14 AR ARP160100084A patent/AR103412A1/es unknown
- 2016-01-14 MA MA041341A patent/MA41341A/fr unknown
- 2016-01-14 TW TW105101030A patent/TWI700274B/zh active
- 2016-01-15 UY UY0001036518A patent/UY36518A/es unknown
- 2016-01-15 DK DK16700810.1T patent/DK3244886T3/da active
- 2016-01-15 UA UAA201708393A patent/UA123002C2/uk unknown
- 2016-01-15 CA CA2972329A patent/CA2972329C/en active Active
- 2016-01-15 SI SI201631406T patent/SI3244886T1/sl unknown
- 2016-01-15 WO PCT/EP2016/050715 patent/WO2016113371A1/en active Application Filing
- 2016-01-15 SG SG11201705760XA patent/SG11201705760XA/en unknown
- 2016-01-15 HU HUE16700810A patent/HUE057299T2/hu unknown
- 2016-01-15 MY MYPI2017001005A patent/MY187068A/en unknown
- 2016-01-15 HR HRP20211782TT patent/HRP20211782T1/hr unknown
- 2016-01-15 LT LTEPPCT/EP2016/050715T patent/LT3244886T/lt unknown
- 2016-01-15 BR BR112017015123-5A patent/BR112017015123B1/pt active IP Right Grant
- 2016-01-15 US US15/542,735 patent/US10029984B2/en active Active
- 2016-01-15 ES ES16700810T patent/ES2904575T3/es active Active
- 2016-01-15 KR KR1020177019398A patent/KR102509848B1/ko active IP Right Grant
- 2016-01-15 EP EP16700810.1A patent/EP3244886B1/en active Active
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